N-nitro-n-methylglucamine pentanitrate



Filed Oct. 17, 1967 FIG.. 2

J w LAWRENCE v N-NITRom-METHYLGLUCAMINE PENTANITRATE FIG. 3

FIG.

INVENTOR Joseph W. Luwfence -BY United States Patent O 3,491,140 N-NITRO-N-METHYLGLUCAMINE PENTANITRATE Joseph W. Lawrence, Lexington, Ohio, assignor to Atlas Chemical Industries, Inc., Wilmington, Del., a corporation of Delaware Filed Oct. 17, 1967, Ser. No. 675,860 Int. Cl. C07c 77/02 U.S. Cl.. 260-467 7 Claims ABSTRACT OF THE DISCLOSURE A method is disclosed for preparing new N-nitro-N- lower alkyl glucamine pentanitrates. These new compounds possess explosive characteristics similar to pentaerythritol tetranitrate (PETN) and may be similarly employed in explosive devices such as primers, boosters and explosive initiators.

This invention relates to N-nitro-N-lower alkyl gluca mine pentanitrates and more particularly to a method of preparing compounds of the formula:

lllNOz H ONOz OZNOCH H ONOz H ONOa (IEHzONOz wherein R is either straight or branched chain lower alkyl of l to about 6 carbon atoms and exemplified by methyl, ethyl, n-propyl, n-butyl, and other similarly related radicals. The present invention also relates to improved ignition devices such as detonators, squibs, primers, boosters and the like containing as a component, the present N- nitro-N-lower alkyl glucamine pentanitrates.

Base charges for use in explosive initiators typically include pentaerythritol tetranitrate (PETN), which may be classified as a secondary high explosive as contrasted to primary high explosives such as mercury fulminate and lead azide.

It has now been found that a new series of compounds which possess similar sensitivity and explosive characteristics to PETN may be prepared by the method of the present invention. The compounds of the present invention may thus be employed in explosive devices such as primers, boosters and explosive initiators.

The compounds of the present ,invention may be readily prepared by first nitrating with, for example, nitric acid, a N-lower alkyl glucamine compound of the formula:

H OH HOCH HOH HCOH

CHQOH ICC to form N-nitrato-N-lower alkyl glucamine pentanitrate of the formula:

wherein R is lower alkyl as previously defined.

The nitration step may be performed by using nitric acid vacuum-distilled from mixed nitric-sulfuric acids to avoid adding water to the nitrating system. A dehydrating agent such as acetic anhydride or sulfuric acid may also be included as a compound of the nitrating step to further limit the inuence of water in the nitrating system.

The nitrating step is generally carried out at a temperature above 0 C. and more specifically at a temperature of about C. Variations in the reaction conditions are possible but higher temperatures tend to be diflicult to maintain.

The N-nitrato-N-lower alkyl glucamine pentanitrate prepared in the nitrating step may be isolated and denitrate. Desirably, the dehydrating step is performed with a combination of materials such as concentrated nitric acid, zinc chloride, and acetic anhydride. 3 The dehydrating step is generally performed at a temperature above 25 C. and generally at a temperature of about C. Higher temperatures tend to reduce yields and increase the difficulty of controlling the dehydration reaction.

A series of initiators containing the new composition of the present invention may be prepared as illustrated in the accompanying drawing in which like numerals represent the same elements throughout the several views.

In the figures:

FIG. 1 is an enlarged half-sectional view taken as a side elevation and illustrating an electric explosion initiator containing the composition of the present invention as a base charge;

FIG. 2 is an enlarged half-sectional view taken as a side elevation and illustrating a second type electric explosion initiator also containing the composition of the present invention as a base charge;

FIG. 3 is an enlarged half-sectional view taken as a side elevation and illustrating a third type initiator containing the composition of the present invention as a base charge; and

FIG. 4 is an enlarged half-sectional view taken as a side elevation and illustrating a fuse cap containing the composition of the present invention.

FIG. l illustrates electric explosion initiator 8 having shell 10 in which may be positioned base charge 12 formed of the explosive N-nitro-N-lower alkyl glucamine pentanitrate prepared by the method of the present invention. superimposed on base charge 12 is priming charge 14. The priming charge which is normally fired by electric match assembly 16 may include any suitable material such as mannitol hexanitrate, diazodinitrophenol, mercury fulminate, lead azide, or mixtures thereof with oxidizing agents such as potassium chlorate.

Electric match assembly 16 includes electric conductive plates 18 and 20 generally formed of a metallic material such as copper or aluminum and applied upon opposite hydrated to form N-nitro-N-lower alkyl glucamine pentao sides of insulating material base 22 formed of an electric non-conductive material such as, for example, cardboard. Bridge wire 24, which may be embedded in match composition 26, is electrically secured to the lower ends of electric conductive plates 18 and 20. Match composition 26 may include, for example, an ignition composition such as cuprous acetylide, diazodinitrophenol, lead mononitroresorcinate, mixtures of lead mononitroresorcinate and potassium chlorate, and related materials and mixtures thereof which may be applied in any convenient fashion, as desired. The ignition composition may be applied, for example, in the plastic state with lacquer about the bridge wire and allowed to harden. A deagrating composition such as mixtures of ammonium picrate and potassium dichromate or carbon and potassium chlorate may also be included as part of match composition 26. One or more coating layers of, for example lacquer may also Ibe included, if desired, when the match composition is formed as a match head.

Opposite match composition 26 are lead wires 28 and 30 which are connected, as illustrated, to the upper ends of electric conductive plates 18 and 20 by a suitable solder material 31. Lead wires 28 and 30 may be coated with a suitable insulating material such as polyvinyl chloride, if desired.

Sealing plug 32 is illustrated at one end of shell 10 for supporting lead wires 28 and 30. The sealing plug may be formed of any suitable material such as rubber, neoprene, or other material which is sufficiently elastic for insertion into shell during assembly.

FIG. 2 illustrates a second type electric explosion initiator 33 having shell 34 containing base charge 12 formed of N-nitro-N-lower alkyl glucamine pentanitrate. Bridge wire 36, embedded in match composition 26 is electrically connected to lead wires 28 and 30 within sealing plug 32.

FIG. 3 illustrates a third type initiator 39 having shell 40, cap portion 42 inserted into shell 40, base charge 12 formed of N-nitro-N-lower alkyl glucamine pentanitrate positioned within shell 40 and in igniting position to match composition 26. Bridge wire 44 of high electrical resistance wire is embedded in match composition 26 and is electrically connected to electrodes 48 and 50- secured in plug 52.

FIG. 4 illustrates fuse cap 54 having flash charge 56 superimposed on primer charge 14 and base charge 12.

Other variations of initiators in addition to those illustrated as well as explosive primers and boosters are also possible devices for using the composition of the present invention.

In order to further illustrate the present invention the following examples are given.

EXAMPLE l 3.9 grams of N-methyl glucamine was added to 21 ml. of concentrated nitric acid at a temperature maintained between 0 C. and about 5 C. Thereafter, 13.5 m1. of acetic anhydride was added and the nitration mixture was heated to 30 C. for 20 minutes and drowned in 100 grams of crushed ice. A granular product was formed. The solid product was washed with water and dried under vacuum. 8.5 grams of white granules melting at 115 C. resulted having an actual percent by weight nitrate nitrogen content of 17.25. The product was identified to be N-nitrato-N-methyl glucamine pentanitrate (CqHlaOlsNq) which has a calculated percent by weight nitrate nitrogen content of 17.39. A dehydration mixture was prepared consisting of 0.6 gram of concentrated nitric acid, 0.5 gram of zinc chloride and 25 grams of acetic anhydride. At a temperature of about 25 C., 4 grams of the prepared N-nitrato-N-methyl glucamine pentanitrate was added to the dehydration mixture. This mixture was next heated to a temperature of about 50 C. for rive minutes. The

mixture was then cooled and poured into 60 ml. of ice water wherein a granular powder formed immediately. The cold suspension was stirred for one hour and the solids were removed by filtration. After washing with water and drying under vacuum, 3.3 grams of white powder were recovered. The recovered powder was found to melt at 102 C. and was found to have an actual percent by weight nitrate nitrogen content of 15.04. The product was identified to be N-nitro-N-methyl glucamine pentanitrate, Which has a calculated percent by weight nitrate nitrogen content of 15.06.

EXAMPLE 2 Two compound detonators similar to that of FIGURE 4 were prepared in 2-inch gilding metal tubes 54 of 0.22 inch inside diameter, employing as base charge 12 in each, 0.30 gram of N-nitro-N-methyl glucamine pentanitrate pressed with 150 pounds on an 0.216 inch diameter pin; as primer charge 14, 0.13 gram of mannitol hexanitrate; and, as flash charge 56, 0.06 gram of a 75/25 mixture of diazodinitrophenol and mannitol hexanitrate pressed with 25 pounds on a 0.216 inch diameter pin. The height of the total charge was about 4%.; of an inch. The loaded detonators Iwere fused in standard fashion, and each primed into a 11/1.l x 8" stick of a. high ammonium nitrate-nitroglycerine dynamite, and shot. Complete detonation was effected. Ten detonators prepared Over this formula were test-fired in the standard lead plate test, resulting in 10 A plates. N-nitro-N-methyl glucamine pentanitrate thus functioned satisfactorily as the base charge in a compound detonator.

It is understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from this invention.

What is claimed is:

1. N-nitro-N-lower alkyl glucamine pentanitrate.

2. The compound of claim 1 wherein the lower alkyl group contains from 1 to about 6 carbon atoms.

3. N-nitro-N-methyl glucamine pentanitrate.

4. A method for preparing N-nitro-N-lower alkyl glucamine pentanitrate which comprises:

(A) nitrating N-lower alkyl glucamine to form N-nitrato-N-lower alkyl glucamine pentanitrate and (B) dehydrating Nr-nitrato-N-lower alkyl glucamine pentanitrate to form N-nitro-N-lower alkyl glucamine pentanitrate.

5. The method of claim 4 wherein nitrating of N-lower glucamine is effected by concentrated nitric acid at a temperature of about 30 C.

6. A method for preparing lN-nitro-N-lower alkyl glui camine pentanitrate -Which comprises:

UNITED STATES PATENTS 3,179,050 4/1965 'Grillith 102-28 3,286,628 1l/1966 Young et al 102-28 3,373,185 3/1968 Wendt et al. 260-467 LELANlD A. SEBASTIAN, Primary Examiner 

